


Dean's List

by Sintari (OriginalSintari)



Series: Sintari's Wincestmas 2019 Ficlets [2]
Category: Supernatural
Genre: First Time, M/M, PWP, Teasing
Language: English
Status: Completed
Published: 2020-01-09
Updated: 2020-01-09
Packaged: 2021-02-27 12:40:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 956
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22187221
Author URL: https://archiveofourown.org/users/OriginalSintari/pseuds/Sintari
Summary: Sam has something of Dean's. Dean's going to get it back.
Relationships: Dean Winchester/Sam Winchester
Series: Sintari's Wincestmas 2019 Ficlets [2]
Series URL: https://archiveofourown.org/series/1597102
Comments: 14
Kudos: 98





	Dean's List

**Author's Note:**

> To some of y'all, I'm really sorry for the ridiculous pun in this title. 
> 
> Written for the lovely [Caffeinechesters](https://archiveofourown.org/users/caffeinechesters/pseuds/caffeinechesters) for Wincestmas 2019/2020.

“Dean. What is this?” 

If Sam isn’t mistaken, his brother looks a little embarrassed when he sees the scrap of green paper in Sam's hand, but in characteristic Dean Winchester fashion he quickly composes his face into a leer.

“What do you think it is?” 

“Well, it’s a list of states with names next to each one. It looks like a sex list.”

“Ding, ding, ding.”

“Oh my God, Dean. Why?”

Dean points vaguely at the TV in their motel room. “Oprah says goal setting is really important for a fulfilled life.” 

Sam rubs his temples. “Since when did you-? You know what. Never mind.” He tosses the list back into the pile of papers he’d been sorting through. Then, unable to help himself, picks it up again, holding it by the corner like it’s a piece of litter he’s gathered off the sidewalk. “This is a lot of names.” 

“Forty-seven.” 

“So, you’re going for blackout bingo on the Lower Forty-Eight.” 

“Yep.” 

“And it looks like… ah. Wyoming.” 

“It’s a lightly populated state. And, surprisingly, not very haunted.”

Sam knows he shouldn’t harp on this, but honestly, he’s flabbergasted. He knew his brother had a prodigious sex life, but he’s never seen it in front of him in black and white (and blue, red, and green ink) before. 

All these names. And not one of them Sam. Not like that would ever be a possibility. Because Dean is straight. Unlike Sam. And Dean is good. Also unlike Sam, who sometimes can’t even breathe when he looks at his brother.

Sam spots something then. “Molly in Delaware. Wait. Molly Cheshire? Our babysitter?” 

Dean’s flipping channels now. “Your babysitter.” 

Sam keeps reading. He’s unable to stop himself. It’s like watching a slow motion train wreck. Then a name makes his heart miss a beat.

“Josh?” 

And suddenly Dean’s up from the bed, wrestling Sam for the paper. 

“All right. That’s about enough of that.” 

But Sam presses his height advantage, balling the paper up in his fist and – satisfyingly – managing to keep it away from his brother’s grasping hand. 

But Winchesters are dirty fighters. Dean tickles his armpit, and Sam reflexively jerks, bringing his closed fist into Dean’s reach. His brother is now prying at his fingers, and so Sam does the only thing he can think to secure his treasure and stuffs it into his pants. To be more precise, in his boxer briefs. 

Oof. Now Dean’s taken out the back of his knee, and Sam falls backward on the bed, barely wrenching his hand out of his jeans in time to stave Dean off as his brother crawls on top of him, pinning his wrists next to his head. 

And now there’s a problem. Sam’s flat on his back on a diamond-patterned motel bedspread, trapped in the cage of Dean’s arms and legs. It brings back memories of sparring, complete with the familiar stirring low in Sam’s belly right next to where Dean’s list is still safely ensconced. He’s so shocked all he can do is peer up at his brother to ensure he isn’t aware of the rapidly growing problem between them. 

But when does Sam Winchester ever get lucky? “Uh oh,” his brother growls down at him, low and animal. “You’re in a predicament now.” 

Sam’s panting a whole lot more than that minimal amount of exertion calls for. But then again, so’s Dean. He could twist against Dean’s thumbs, or swing a knee right up into Dean’s junk, but the way his brother is looking down on him has him docile as a kitten.

Then his brother’s eyes flick to Sam’s crotch.

…Oh, his list. He’s just looking for his list. The disappointment bubbles in Sam’s chest. And the way Dean’s looking at him isn’t helping.

“Give it to me,” his brother husks.

Sam surprises himself. “What if I don’t?” 

“Oh, I’m going to get it one way or another.” 

“Then get it.” 

Sam never thought it would be like this, the first time his brother unzipped his jeans. He never thought it would happen at all. But now here he is, spread out under Dean like wide open countryside, fly gaping open, blue and green plaid boxer briefs on display, and his cock bobbing in the no man’s land between them. 

One of his hands is free. He could escape now, of course. Easily. But instead Sam blinks in shock when his brother, still staring down at him, slowly runs his tongue over his bottom lip. 

“Now where is it?” Dean asks rhetorically. He’s easing Sam’s waistband down over his hipbone, the world’s slowest search. “Hmmm. Not here.” 

Sam’s mortified when a jet of precome escapes, darkening a circle at the spot where the head of his cock tents his boxers. 

His eyes are darting between Dean’s face and his hands. His brother has gone shark-eyed, but his lips are curled into the barest of smiles. Sam’s mesmerized. 

Dean moves on to the other side now, ignoring his straining cock. This time, Dean’s thumb slots into the ridge of hipbone there. Reflexively, Sam lifts his ass off the bed. 

His brother takes his time. The waistband of Sam’s boxers catch on his head, and he feels them smearing with his precome. Then he’s freed, and his brother – his big brother – is easing his boxers down around his thighs. They both watch as the list, now balled up and flattened, topples onto the bedspread. 

“You’re in so much trouble.” 

Oh Sam knows. 

He swallows. In for a penny. “What’s my punishment?” 

Dean reaches up and runs the barest tip of one finger up the underside of Sam’s aching cock. 

“That’s the last time that gets touched.” A pause. “Until we get to Wyoming.”

**Author's Note:**

> Comments and kudos are love. Come play with me on [the Tumblrs](https://crooked-sleep.tumblr.com/post/189694659249/supernatural-mostly-wincest-fic-master-list-i)!


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